(IUCr) (3R,5S)-5(3)-Carboxy-3,4,5,6-tetrahydro-2H-1,4-thiazin-4-ium-3(5)-carboxylate

Volume 64
Part 3
Page o636
March 2008

Received 12 February 2008
Accepted 22 February 2008
Online 27 February 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.032
wR = 0.095
Data-to-parameter ratio = 13.9
Details

(3R,5S)-5(3)-Carboxy-3,4,5,6-tetrahydro-2H-1,4-thiazin-4-ium-3(5)-carboxylate

Gustavo Portalone,^a ^* Alberto Cassetta,^b Marcello Colapietro ^a and Susanne Heidi Plattner ^a

^aChemistry Department, University of Rome I "La Sapienza", P.le A. Moro 5, I-00185 Rome, Italy, and ^bInstitute of Crystallography, CNR, Trieste Outstation, Area Science Park-Basovizza, S.S.14 Km 163.5, I-34012 Trieste, Italy
Correspondence e-mail: g.portalone@caspur.it

The molecule of the zwitterionic title compound, C₆H₉NO₄S, which lies on a mirror plane, shows a puckered chair conformation of the six-membered ring with the S and N atoms out of the mean plane of the other four C atoms by 0.929 (2) and 0.647 (2) Å, respectively. The ionized carboxyl group is equatorially oriented. The hydrogen-bonding network includes very short O-HO [2.470 (2) Å] and N-HS [3.471 (2) and 3.416 (2) Å] intermolecular contacts.

Related literature

For the detection of 1,4-thiomorpholine-3,5-dicarboxylic acid (THT) as a normal component in bovine brains and human urine, see: Cavallini, Pecci et al. (1985); Cavallini, Matarese et al. (1985); Matarese et al. (1987); Cavallini et al. (1991). For the previous structure determination of the (3R,5R) epimer of THT, see: Portalone et al. (1993). For related literature, see: Allen et al. (1997); Paglialunga Paradisi et al. (1990).

Experimental

Crystal data

C₆H₉NO₄S
M_r = 191.21
Orthorhombic, P b n m
a = 6.1641 (8) Å
b = 9.323 (1) Å
c = 12.760 (1) Å
V = 733.29 (14) Å³
Z = 4
Mo K radiation
= 0.41 mm^-1
T = 298 (2) K
0.20 × 0.15 × 0.10 mm

Data collection

Huber CS four-circle diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.916, T_max = 0.958
1840 measured reflections
1060 independent reflections
998 reflections with I > 2(I)
R_int = 0.02
3 standard reflections every 97 reflections intensity decay: 2%

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.094
S = 1.07
1060 reflections
76 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.25 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O1ⁱ	1.24	1.24	2.4704 (19)	180
N4-H41S1ⁱⁱ	0.87 (3)	2.60 (3)	3.4713 (15)	179 (3)
N4-H42S1ⁱⁱⁱ	0.80 (3)	2.72 (3)	3.4155 (16)	147 (3)
Symmetry codes: (i) -x, -y-1, -z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: XCS (Colapietro et al., 1992); cell refinement: XCS; data reduction: XCS; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: WinGX.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2198 ).

Acknowledgements

We thank MIUR (Rome) for 2006 financial support of the project `X-ray diffractometry and spectrometry'.

References

Allen, F. H., Bird, C. M., Rowland, R. S. & Raithby, P. R. (1997). Acta Cryst. B53, 696-701.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Cavallini, D., Matarese, R. M., Pecci, L. & Ricci, G. (1985). FEBS Lett. 192, 247-250.
Cavallini, D., Pecci, L., Matarese, R. M., Ricci, G. & Achilli, M. (1985). J. Biol. Chem. 260, 15577-15579.
Cavallini, D., Ricci, G., Dupré, S., Pecci, L., Costa, M., Matarese, R. M., Pensa, B., Antonucci, A., Salinas, S. P. & Fontana, M. (1991). Eur. J. Biochem. 202, 217-223.
Colapietro, M., Cappuccio, G., Marciante, C., Pifferi, A., Spagna, R. & Helliwell, J. R. (1992). J. Appl. Cryst. 25, 192-194.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Matarese, R. M., Pecci, L., Ricci, G., Nardini, M., Antonucci, A. & Cavallini, D. (1987). Proc. Natl Acad. Sci. USA, 84, 5111-5114.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Paglialunga Paradisi, M., Pagani Zecchini, G., Torrini, I. & Lucente, G. (1990). J. Heterocycl. Chem. 27, 1661-1664.
Portalone, G., Cassetta, A., Pagani Zecchini, G. & Torrini, I. (1993). Acta Cryst. C49, 976-978.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds